Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Communication | Regular issue | Vol 29, No. 12, 1989, pp.2253-2256
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5156
Studies on as-Triazine Derivatives XIV. Synthesis and Reverse Electron-demand Diels-Alder Reaction of Ethyl 5,8-Dichloro-1,2,4-benzotriazine-3-carboxylate

Mataichi Sagi, Osamu Sato, Shoetsu Konno, and Hiroshi Yamanaka*

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Ethyl 5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate was treated with sulfuryl chloride to give ethyl 5,5,8,8-tetrachloro-5,6,7,8-tetrahydro-1,2,4-benzotriazine-3-carboxylate. Following dehydrochlorination of the tetrachloro compound with triethylamine afforded ethyl 5,8-dichloro-1,2,4-benzotriazine-3-carboxylate. The dichloro-1,2,4-benzotriazine derivative was heated with norbornadiene in p-cymene to give ethyl 5,8-dichloroquinoline-2-carboxylate. Intramolecular Diels-Alder reaction of the dichloro-1,2,4-benzotriazine derivative was also investigated.